


Taking a Chance

by Muykke



Series: Taking Chances [1]
Category: Teen Wolf (TV)
Genre: Derek Hale is Bad at Feelings, Loss of Virginity, M/M, Plot What Plot/Porn Without Plot, Stiles is 17, Underage Sex
Language: English
Status: Completed
Published: 2018-05-24
Updated: 2018-05-24
Packaged: 2019-05-13 07:00:04
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,070
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14744120
Author URL: https://archiveofourown.org/users/Muykke/pseuds/Muykke
Summary: The story of how Stiles suddenly realizes he's attracted to Derek and what are they going to do about it.





	Taking a Chance

**Author's Note:**

> A fantasy that could have taken place "behind the scenes".
> 
> This is my first fanfic ever. Hope you'll enjoy reading it! All the comments are welcome!
> 
> Also this is the first part of the series, so if you like it, stay tuned for the update!
> 
> P.S. Thanks to Unne for being my beta.

If only a month ago someone told Stiles that this is going to happen to him, he wouldn't have believed it. He would have laughed and probably said that a person implying such a thing was mad.

Now it didn't seem that crazy. Stiles got obsessed with Derek Hale. Like really bad.

They had known each other for quite some time, but Stiles never had any fantasies about Derek before. Not to mention body reactions. Stiles had always thought he was into girls. He had been in love with Lydia for God knows how long. He was sure he was still in love with her, regardless. But this was different somehow. This obsession penetrated his thoughts one day and never left ever since.

The first time it happened, he waived it. But now every single day Stiles had to deal with an awkward boner. Sometimes several times a day. It was rather understandable since he was a horny 17-year-old boy. But such things never happened when he was thinking about Lydia or, god forbid, other girls (never). And frankly, by the end of this "permanent-hard-on" month, Stiles got really frustrated. Only yesterday he saw Derek at the school parking lot. They didn't say a word to each other but Stiles was ogling Derek like a maniac and then had to lock himself in the boys' restroom to quickly get off while thinking of Derek working out shirtless. There was a slight possibility that Stiles could be gay after all. Never mind his wardrobe preferences. Or at least bi. Or maybe he was just gay for Derek. Damn it.

Now he was sitting in his room trying to concentrate on his homework. All he managed to concentrate on was how Derek sat on this very chair during his last hiding, reading a book, then grumbling about Stiles' shirt that wouldn't fit. Over a year passed since that, and many things happened after, so why was Stiles remembering this now? And getting hard again. Perhaps some creepy mythical creature secretly bit him or some Cupid-witch cursed him with everlasting erection over Derek Hale and messed up his memories. You never know what could happen in Beacon Hills these days.

He had to jerk off again (it became a routine now) and went down to the kitchen to pour himself some milk, that hopefully would help him go to sleep. He took a large sip while going up the stairs when suddenly he heard his computer chair squeak. The chair was old and made a lot of various noises, but Stiles got so used to it that he didn't want to get rid of it. And now it squeaked. There. While he stood on the stairs in front of his door with a glass of warm milk. And his bat was comfortably standing next to his bed, in his room, where the goddamn chair had just squeaked. Perfect.

All right, calm down, Stiles told himself. Whoever or whatever it was, he can splash it with milk first and then either run for his bat or run away screaming. Right as Stiles was bracing himself up, he heard a squeak again - this time from the floor. Someone stepped on an old floorboard. The only floorboard in the room that needed fixing, was right beside the door. So there definitely was someone in his room and they were one door away from each other... Not letting Stiles a moment to come up with something better than a "milk-splashing plan", the intruder threw the door open.

"FUCK! Stiles! The fuck's wrong with you?!" Derek was yelling, trying to throw the last drops of milk off his leather jacket. Milk was dripping from his face, drenching his t-shirt.

"What's wrong with YOU? Sneaking up like that! I almost got a heart attack! What are you doing in my house anyway?"

"The Hunters are raiding again. Scott suggested I stay at your place till they're gone. They won't be looking for me here." He paused, thrown off by Stiles' overwhelmed face.

"That's if you don't mind of course." He added. "Hasn't Scott told you? He told me he would. Damn it!" Derek took off his jacket. "Who even drinks milk at night? What are you? Ten?"

Stiles preferred not to answer and checked his phone. Battery dead. Great. So Scott couldn't reach him and sent Derek to him anyway. Well probably that was smart - if something had happened to Stiles, Derek could help, and if everything was okay, he could successfully hide for the night at his place. Clever Scott, as always.

Meanwhile, Derek took off his damp shirt as well. Holy Christ. What are the chances? Derek is in his room for the second time ever and he has to take his clothes off again.

"I'm gonna wash up." The werewolf said and went off to the bathroom leaving Stiles with a rapidly beating heart, an empty milk glass, and an awakening hardness in his pants.

That was "perfect" timing. Stiles hoped he would not embarrass himself while Derek was here. One night. Just one night. And hopefully, they will spend it sleeping. Separately. Right. Oh, dear God! Derek walked in shirtless, and Stiles immediately had to sink into the chair and cross his legs.

"I need something to change. Anything will do. Unless you'd prefer me here without a shirt." Derek chuckled.

Stiles swallowed hard, trying to come up with some clever answer. Anything, so he doesn't have to get up to fetch Derek a new t-shirt and reveal the fact that he has a huge hard-on. In front of Derek Hale. That would be the new definition of awkward.

"Are you okay?" Derek asked cautiously." You're so pale. And sweating like you have a fever, but you don't."

_Keep calm or he'll suspect something. And not necessarily the most obvious thing. Too late._

"Why are you scared? I can tell: your heart is racing. And pupils dilated." Derek stepped closer. No doubt he's now considering some outside danger. Like maybe there are Hunters in the house or something like...

"Stiles?.." Derek closed his eyes sniffing the air.

"Yes, Derek?" Stiles tried to make his voice as calm and steady as possible.

"I can't smell anyone else here."

_What is he getting at?_

"There's no one else. Just you and me."

"Right." Derek opened his eyes and looked straight at Stiles. "And you are sexually aroused."

_Shit._

"If there's no one here now - and hasn't been for a while, I can tell, then..."

"Then?"

Derek stepped a couple steps back. Stiles turned red and hid his face in his palms trying to shake off an overwhelming sense of embarrassment.

"I'm sorry." He muttered. "You shouldn't have known. I would have never told you. Gosh.. This has got to be the most awkward situation I've ever been in, and you know  _me_... Oh,  fuuuck."

"Stiles, look at me."

The boy took his hands off his face. Derek was standing in front of him, handsome and serious, and shirtless, and saying the most unbelievable words:

"I can think of a couple of things that would help you with it." He smiled with a corner of his lips.

"Wha.." Stiles couldn't make a proper sentence to ask what he really wanted to. Whether Derek meant sex stuff or some weird werewolf ritual crap?

"I mean sex." Derek said bluntly.

All Stiles managed to answer was a nervous chuckle. Of course, keen werewolf senses told Derek everything about him, but how could he be suggesting such a thing in the first place?

"I've never thought you were gay." Stiles finally came to his senses.

Derek paused as if choosing the right answer.

"I'm not gay. I fuck guys sometimes. When I feel like it."

"Yeah, right. Like that's really a thing."

"Shut up and take off your clothes." Derek ordered calmly, but with just the right amount of menace in his voice. Like he always did.

Stiles paused for a moment, considering if he might be having an auditory hallucination. But Derek brought him out of his stupor by taking his trousers off. He wasn't wearing any underwear.

"Well? Are you going to stand there and look at me forever?"

Stiles stood up and clumsily started taking his shoes off, muttering something like "why not to look if there's so much to look at".

When their clothes finally came off Stiles had two thoughts. Firstly, Derek was looking so damn hot naked (not that he had any doubts about it before), and Stiles' boner sustained it. Secondly, to his surprise, Stiles wasn't feeling awkward being naked in front of another guy. Hell, he could appear naked in front of Derek Hale any time and be totally cool with it.

Derek jerked his head to the side, wordlessly telling Stiles to get on the bed. Stiles took several longest steps in his life before he reached his bed and sat on the blanket.

"Turn around. Lie down." Derek ordered.

Stiles felt a little thrown off by the cold tone of his voice, but did as he was told. Derek wasn't known for his gentleness after all. Lying facedown, Stiles got a start of surprise when Derek's hot palm touched his back and started slowly caressing him up and down. That felt nice and was really soothing and relaxing. Stiles wondered if Derek would kiss him. That's customary for people to kiss during sex, right? But apparently, Derek didn't think so. His lips didn't touch Stiles once. But his hand was getting lower and lower until it reached his crotch.

"Spread your legs a bit." Derek's voice sounded from behind.

Stiles tensed up a little when Derek's wet finger entered him and then tensed a little more when Derek put his second finger in. If Derek's erect cock was any bigger than his two fingers (let's hope for that), the sex promised to be quite painful. Luckily Stiles was in a right position to stretch his hand under the bed and fish out a jar of body lotion. Because what teenage boy doesn't have a lotion handy.

Stiles passed the jar somewhere backward without looking, hoping that Derek would get the hint and use it. Derek obliged. Next time the fingers entered Stiles' body, they were slick and hot and moved gently and... Oh my god! What was that magic spot?! Stiles caught his breath and moaned. Derek approved by adding his third finger and going right for that spot that felt sooo damn good.

After a while of Derek's manipulations, Stiles got all drugged with pleasure and felt it tingling in every cell of his body. Derek kept stroking him inside and it felt so right and pleasant that Stiles realized he is going to come quite soon. He didn't want it to happen just yet, so he caught Derek's wrist to make him stop.

"You better get to the business right away. I'm too close." He said quietly.

Derek bend forward so that Stiles felt his naked chest touching overly sensitive skin on his back.

"Not that soon. Not until I'm done with you." he whispered into Stiles' ear almost making him squeak with anticipation. The boy's cock was so hard and demanded attention but Stiles wasn't sure if Derek would approve if he touched himself. He wouldn't mind Derek take care of his cock since he did all that amazing job with his hands so far, but Stiles didn't dare ask.

"I need you to say it. Outloud." Derek whispered sternly.

"What?" Stiles was so nervous that it seemed he had forgotten all the sensible words and there was only moaning left to express his agreement.

"That won't do. Say it. Say you want it."

"I... I want it." Stiles forced out, in an unsteady voice. He was afraid Derek would think he didn't want to go further, that he had said "yes" out of fright of being intimidated by the older guy. And not any guy - a big bad grumpy werewolf - essential Derek at his finest.

"I do want it, Derek. Please." Stiles added almost begging.

Derek didn't answer. Not with words. He moved closer, almost covering Stiles' body with his, and after a moment the boy felt Derek's cock slowly entering his body.

Fuck, that hurt. No fingering, however precise, could ever prepare him for this new sharp burning sensation like someone sticking a hot iron rod up his ass. And there also was an overwhelming feeling of another person being inside his body, moving at his own will. Stiles buried his face into the blanket, gripping it firmly. He tried to move away involuntarily, but Derek steadied him by the shoulder and moved his dick a little bit out. Stiles was panting unsteadily, trying to cope with the novelty of it all.

"Shhh. Calm down." Derek whispered gently. "Pain is the part of the process. It'll go away."

Stiles relaxed a little, putting himself in the hands of the man in charge. And then Derek thrust pushing his dick further inside. And then again. And again. And then he wouldn't stop. Stiles clenched his teeth trying to suppress a cry. Why did he ever agree to that?

But after some time of painful thrusts, Stiles began to realize, that the pain had subsided a little and a nice pleasant sensation started taking its' place. Stiles' grunts of pain changed into little cries of pleasure. With every Derek's thrust, Stiles felt his insides being stretched and filled and it felt so good. It burned too but Stiles was getting used to it. Each time Derek's cock stroked this magic spot inside him, little stars appeared in front of Stiles' eyes and danced under his skin. All this felt both good and bad and a little wrong.

Although what could be wrong about Derek Hale's fit muscular body moving over him, his strong hairy arms pressing him into the mattress, his hard cock moving inside him in steady rhythm? No. This became a total bliss, however painfully and awkwardly it had started. Stiles wondered if this was a "one time only" thing or they could repeat it some other time. There was no way of saying. He could hardly believe they were doing this right now. Whatever, he must enjoy this time as if it was their one and only.

He propped himself on his elbows and turned his head, willing to see the werewolf’s face. Derek looked stern. He was silent and somewhat aloof as if he was performing a serious task and didn't want to be distracted. Of course, he looked like that most of the time, but they were having sex for God's sake! Didn't it make any difference to him at all? That's not how it should be, Stiles thought. Why was Derek so tense? He wasn't the one taking it up the ass after all. A quick thought crossed Stiles' mind. He turned his face to Derek once again and gave a long moan of pleasure, trying to sound as convincingly as he could.

"That's it, that's so good, please go on." He added in the softest voice.

And that did the trick. Derek stopped moving, leaned it and put his left arm around Stiles' chest, lifting him up a bit and pressing him firmly against his own chest. He buried his face in the back of the boy's neck and resumed his thrusts. And then Derek let go of his voice too. First, there were short groans and then they became louder and longer. As if he'd been waiting for the Stiles' encouragement. Could it be that he was just worried that he'd been hurting Stiles and now when he knew the boy enjoyed it, he could let go? Possibly. Stiles relaxed completely, knowing that Derek enjoyed their shared experience too. He finally felt that their desire, arousal and all the reactions were mutual like they were together in this, not two separate people in their own thoughts. And everything got so much better.

And so they moved rhythmically, breath uneven, hair damp with sweat, eyes shut, hot skin on skin, legs entwined, both groaning and panting loudly in unison.

They could wake every neighbor, alive or dead if there were any. Thank God, Sheriff Stilinski was at work. But under circumstances, if his father was to walk in on them right now, Stiles wouldn't even care. He was too close to the finish.

"I'm gonna... I'm gonna..." Stiles couldn't catch his breath, but there was no need.

Derek was getting close too. His thrusts became fast and frenzy, groans started resembling roars. So close. Any moment now. Stiles felt like all his pleasure and pain, burning and tension, joy and happiness merged into one tiny ball. He shut his eyes and stopped breathing for a moment. And suddenly the ball exploded with every pleasant sensation he could ever imagine. Stiles arched his back, gave the loudest moan of pleasure and release and dropped himself face down on the bed, utterly exhausted.

Derek gave a last thrust, made a loud roar (almost human), stuck his nails into the mattress and collapsed on Stiles' back breathing heavily. Stiles lay under him, enjoying the way the heavy body was covering him like a blanket. As the stars were dancing in front of his eyes, Stiles couldn't know that only a second ago Derek's nails turned into sharp talons, ripping through the mattress, that he bit through his lip trying to suppress the rising werewolf and was now dripping blood between Stiles' shoulder blades. He didn't know that he was just a moment away from the danger, but was spared.

They lay naked side by side on the bed, eyes closed, but not sleeping. Derek was recuperating, so he could go out there and be in his full strength, just in case.

Stiles was remembering all the things that happened. And all these other thoughts were running through his mind. Should he tell Scott or keep it a secret? Will anyone notice that he has had sex when he comes to school tomorrow? Suppose not, as long as he's able to walk straight after that. No pun intended. Will they do it again? What is Derek thinking right now? What would it be like if they kissed?

And just like that, imagining their kiss, Stiles dove into sleep with a little smile on his face.

**Author's Note:**

> Thanks for reading!
> 
> All the reviews are welcome, so please leave a comment if you have anything to say. But be polite :)
> 
> Also this is the first part of the series, so if you like it, stay tuned for the update!


End file.
